Synthesis from sucrose

Irvine, F.R. Woody Plants of Ghana Cambridge University Press London, 1961. 

Takeno, H. Hashimoto, M. Chem. Pharm. Bull. 34 (1986) 2642. 

Regehng, H. RouvrUe, E.D. Chittenden, G.LF.Recl Trav. Chim. Pays-Bas 106 (1987) 461. 

Hugemer, M. VaseUa, A. Helv. Chim. Acta 71 (1988) 609. 

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F. Ouame and A. Guibert, Fmcto-oligosaccharides Enzymatic synthesis from sucrose, Zuckerind, 120 (1995) 793-798. 

G. Gradnig, G. Legler, and A. E. Stutz, A novel approach to the 1-deoxynojirimycin system Synthesis from sucrose of 2-acetamido-l,2-dideoxynojirimycin, as well as some 2-N-modified derivatives, Carbohydr. Res., 287 (1996) 49-57. 

Ouame F, Guibert A (1995) Fructo-oligosaccharides enzymatic synthesis from sucrose. Zuckerindustrie 120 793-798... 

In Bacillus subtilis and Aerobacter levanicum, levans synthesized with levansucrase (EC 2.4.1.10) are highly branched.197-199 Levansu-crase catalyzes the synthesis from sucrose, as shown in equation 5. 

Synthesis from sucrose 1-Deoxymannojirimycin (2) was synthesized from sucrose by treatment with triphenylphosphine and tetrachloromethane followed by Sn2 displacement of the resulting chloride groups with azide ion to afford the 6,6 -diazido-6,6 -dideoxysucrose 65 in 57% overall yield from sucrose (Scheme 13). Hydrolysis of 65 with ion-exchange resin afforded a mixture of 6-azido-6-deoxy-D-glucose (66) and 6-azido-6-deoxy-D-fructofuranose (67). The azido derivative 66 was converted into 67 in 25% yield... 

Palatinose/ Isomaltulose OS [Glc(al-] 6)Fru Enzymatic synthesis from sucrose... 

Synthesis from sucrose ester/half-ester derivatives, monoepoxide and diisocyanate. Sucrose "penta"-soyate (the methanol insoluble fraction of the soap-free product) was reacted at 100°C for 4 hours with a mixture in xylene of 1 mole equivalent cyclic anhydride e.g., phthalic or tetrahydrophthalic anhydride and monoepoxide e.g., styrene oxide or Cardura E (the glycidyl ester of versatic acid), branched C9-Cfatty acids, in the presence of N-benzyl dimethylamine as catalyst. A faster rate was achieved with the phthalic system. The course of reaction between half ester carboxyl groups and epoxide groups was followed by acid value. About 90% reaction was achieved in all cases and to the product was added 1.0 mole toluene diisocyanate (the meucimum amount without gelation) and dibutyl tin dilaurate as catalyst. 

Synthesis from sucrose ester, aluminium diiso-propoxide monoacetylacetonate and diisocyanate. In pre-liminary experiments, sucrose "penta"soyate or sucrose "penta" dehydrated castor ester reacted in toluene at IIQOC with an equimolar proportion of aluminium diiso-propoxide monoacetylacetonate. (The latter was prepared separately by reaction of equimolar proportions of aluminium isopropoxide and acetylacetone in refluxing toluene with elimination of 1 mole 2-propanol). The modified sucrose ester reacted with 1.1 mole toluene diisocyanate (the maximum without gelation) and dibutyl tin dilaurate as catalyst. The performance of air-dried or stoved coatings was similar to material derived by the mono-/diisocyanate route in terms of alkali resistance, but they were more brittle. 

A fructan. See Fructans, F-43. Prod, comly. by enzymic synthesis from sucrose. Isol. from horse chestnut (Aes-culus hippocastanum), Lycoris radiata, tulips and Leucojum spp., seeds of onions and roots of Asparagus. Low-calorie sweetening agent for food and chewing gum. Constit. of neosugar which improves the intestinal flora in humans. Cryst. (MeOH/EtOH) cryst. 

Buchala A.J. 1987. Acid p-fructofuranoside fructohydrolase (invertase) in developing cotton (Gossypium arboreum L.) fibres and its relationship to P-glucan synthesis from sucrose fed to the fibre apoplast. J Plant Physiol 127 219-230. 

The enzymatic conversion of 6-azido-6-deoxy-D-glucose into its D-fructose isomer was utilised as a key step in a five-step synthesis from sucrose [80] of the natural product and powerful D-mannosidase inhibitor 1-deoxymannojirimycin (l,5-dideoxy-l,5-imino-D-mannitol, 66) [81]. Subsequently, it was shown that the immobilised enzyme from Streptomyces murinus sp. (Sweetzyme T from Novo A/S) was able to isomerise D-glucose derivatives with modifications at C-3 and C-6 such as 6-azido-6-deoxy-3-0-methyl-D-glucose (67) as well as the corresponding 3-deoxy derivative 69 (Scheme 24) [64,82]. 

The aminosugar (42) (see Chapter 9 for its synthesis) was converted to its 6-phosphate (43) via l//-tetrazole-mediated phosphitylation with bis(benzyloxy)-JV,/V-diisopropylaminophosphine, and the D-fructofiiranose 6-phosphate derivative (45) was obtained from the selectively protected precursor (44) (see Chapter 2 for its synthesis from sucrose) by exposure to 2-chloro-l,3,2-dioxaphosphorinane-2-oxide followed by debenzylation. ... 

Levan synthesis from sucrose was found to be strongly inhibited by D-glucose, D-galactose, D-xylose, L-arabinose, maltose, and lactose, but not... 

Inulin (polysaccharide) residues [Fru/32 1]Fru/32 1 Glc with 10-64 [Fru/32 1] synthesis from sucrose Artichokes Yes... 

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